Methane, dichloromethoxy- → 2-Fluoro-4,5-dimethoxybenzaldehyde

Temperature

0 °C

In a flame-dried, round-bottomed flask fitted with a magnetic stirrer and N2 inlet was placed 4-fluoroveratrole (0.78 g, 5.0 mmol, Aldrich Chemical Co.) in 20 ml of anhydrous CH2Cl2. After cooling to 0° C., titanium (IV) chloride (0.91 ml, 1.57 g, 8.3 mmol) was added, followed after 10 min. by a,a-dichloromethyl methyl ether (0.45 ml, 0.575 g, 5.0 mmol). The mixture was allowed to warm to room temperature and after 2 hr it was quenched with an excess of aqueous saturated NaHCO3. The suspension was filtered through a pad of d.e. (diatomaceous earth), the aqueous phase was extracted with additional amounts of CH2Cl2 and the organic phases were combined and washed with water followed by saturated aqueous NaCl. After drying with MgSO4, the organic solvent was removed in vacuo to give the title compound as a white solid, 910 mg.

1. customIn a flame-dried, round-bottomed flask fitted with a magnetic stirrer and N2 inlet
2. temperatureto warm to room temperature and after 2 hr it
3. customwas quenched with an excess of aqueous saturated NaHCO3
4. filtrationThe suspension was filtered through a pad of d.e
5. extraction(diatomaceous earth), the aqueous phase was extracted with additional amounts of CH2Cl2
6. washwashed with water
7. dry with materialAfter drying with MgSO4
8. customthe organic solvent was removed in vacuo

ORD record

ord-cea5963e61c54fcea99b57a43cf1be79

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07084165B2